I'm Sleeping With My 17-Year-Old Babysitter. Help!

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Dear Willie D:

I’m a 39-year-old widower who’s been having sex with my kids’ 17-year-old babysitter for the past year. My kids are toddlers, so they are too young to know what’s going on when we go into the room and shut the door. Although she is gorgeous, this is not something I planned. She is the daughter of a friend.

Her dad inquired about buying an old car of mine for her. So he suggested that I let his daughter babysit, and drive the car while she worked for the money to earn it. The first couple of times she babysat and I came home, things were was normal. We hugged (as we always do in front of her parents), I paid her, and she left.

But the third time, I don’t know what it was but we hugged a little longer, and tighter, and it happened. We started kissing, and had sex. Although she paid the car off months ago, her parents aren’t suspicious because she told them she is now working to have her own money.

They think I get off work at a later time, which gives us time to be together during weekdays in addition to weekends. This is not a fling. I’m in love with her. The thought of going to jail for having sex with a minor scares the hell out of me, but I don’t know how to reverse my feelings. What should I do?

Sex With A Minor:

Because the girl is 17, depending on the state you live in, you might be in the clear to have sex with her legally today, but that doesn’t mean Johnny Law won’t go back to when the girl was a minor and charge you with statutory rape.

If she is still a minor, you need to think about your kids because the state will remove them from your home and lock you up. Even if the girl is of age, she is still a child. She may be great in bed, but she’s not ready for a grownup relationship, and you know that.

And what if her dad, your friend, catches wind of the true nature of your relationship with his little girl? When you love something, sometimes the best thing you can do is set it free. Set her free, man. It’s not worth it.


Dear Willie D:

I told a friend I would sell him my car; now I want to keep it because I realized that I was going to sell it too cheap. He has already sold his car in anticipation of buying mine. How do I break the news to him without hindering our friendship?

Seller’s Remorse:

Just be straight up, and tell him you changed your mind because you realized you were selling the car too cheap, and if he still wants to buy it he can. Then tell him the new price. He might not take it well, but if he’s a true friend he won’t allow it to destroy your friendship.


Dear Willie D:

My stepbrother’s dad (my dad married his mother) controls him through employment. He is 21 years old, and still has to get permission from his dad to leave town. His dad told him he needs to check with him in case he has an emergency job, or another worker doesn’t show up, which is BS.

My stepbrother had a girl who he really liked, but his dad ran her off because he simply didn’t like her. His dad is a narcissist who insults him every chance he gets. Every time he opens his mouth he talks about how stupid or low-life someone else is, and how smart he is or how much money he makes.

He controls my stepbrother because he pays him twice as much as anybody else would pay him to do the same job. The reason I’m writing to you is because my stepbrother told me he was on the verge of a nervous breakdown, and didn’t know what to do about his dad. I’m only 23 years old so my knowledge of this type of thing is not as extensive as yours. How should he go about getting his dad off his back?

Stepbrother’s Defense:

As long as your stepbrother works for his dad, his dad will continue to control him because his dad don’t respect the fact that his little boy is now a grown man. Tell your stepbrother the day he resigns from working for his dad will be the day he resigns from being pushed around.

No amount of money is worth one’s sanity.


Dear Willie D:

I’m concerned about the Obama Administration’s relentless pursuit to regulate. I run a mom-and-pop e-cigarette business, and I’m scared to death that new regulations could lump my products with all tobacco products, and force me out of business.

Unless you smoke e-cigarettes, you could probably care less. But what are your thoughts on the multitude of current regulations, and those yet to come from Obama and his successors?

Scared to Death:

The thing about government regulation is, the only time we have a problem with it is when it contradicts our interests. Regulations are necessary to protect the public, and keep would-be violators in check. The trick is making sure that each regulation is applied with integrity, and does not become tainted by greed and self-interest.

Because let’s face it, lobbyists run America. Every major state and government agency that we rely on to protect us is overrun with corruption – and I do mean every one of them! 

Ask Willie D anything at willied.com/ask-willie-d, and come back next Thursday for more of his best answers.

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